ALKENES

ALKENE
-also called “olefin”.

-is an acyclic unsaturated

hydrocarbon that contains one or
more carbon-carbon double bond.
Functional Group:

C=C
 Alkane and alkene only differ in the
ending.

Alkane- “-ane”
Alkene- “-ene”
General Formula:

CnH2n
Two simplest alkenes

Ethene Propene
(Ethylene) (Propylene)

CH2=CH2 CH =CH-CH3
2
CYCLOALKE
NE
-is a cyclic unsaturated hydrocarbon
that contains one or more carbon-
carbon double bond within the ring
system.
 Cycloalkane Cycloalkene

1,2-dimethylcyclopentane
Cyclopentene
IUPAC Nomenclature
for Alkenes and
Cycloalkenes
 “Find your
Hydrocarbon Love”
Rule 1. Replace the alkane suffix -ane with the suffIx -ene,
which is used to indicate the presence of a carbon–carbon
double bond.

NOTE: “-ene” indicate carbon-carbon double bond

Rule 2. Select as the parent carbon chain the longest

continuous chain of carbon atoms that contains both
carbon atoms of the double bond.

NOT
Rule 3. Number the parent carbon chain beginning at the end
nearest the double bond.

NOT

NOTE: If the double bond is equidistant from both ends of

the parent chain, begin numbering from the end closer to a
substituent.

NOT
Rule 4. Give the position of the double bond in the chain as
a single number, which is the lower-numbered carbon atom
participating in the double bond.

But-2-ene

3-Methylbut-1-ene
Rule 5. Use the suffixes-diene,-triene,-tetrene, and so
on when more than one double bond is present in the
molecule. A separate number must be used to locate each
double bond.

But-1,3-diene 3-Methylpent-1,4-diene
Practice Exercise
Assign IUPAC names to the following alkenes.

a. CH3-CH=CH-CH2-CH-CH3 5-Methylhex-2-ene
CH3
b. CH2=CH-CH=CH2 But-1,3-diene
CH3
2-Methylbut-1-ene
c. CH2=C-CH2-CH3

d. CH2=CH-CH2-CH=CH-CH3 5-Methylhept-1,4-diene
CH2CH3
e. CH2=C-CH2-CH2-CH2-CH=CH2 6-ethyloct-1,6-diene
CH3 CH2CH3
Rule 6. A number is not needed to locate the double bond in
unsubstituted cycloalkenes with only one double bond because
that bond is assumed to be between carbons 1 and 2.

Rule 7. In substituted cycloalkenes with only one double bond,

the double-bonded carbon atoms are numbered 1 and 2 in the
direction (clockwise or counterclockwise)that gives the first-
encountered substituent the lower number. Again, no number is
used in the name to locate the double bond.
Rule 8. In cycloalkenes with more than one double bond
within the ring, assign one double bond the numbers 1 and
2 and the other double bonds the lowest numbers possible.

Cyclohex-1,4-diene 5-Chlorocyclohex-1,3-diene
Practice Exercise
Assign IUPAC names to the following cycloalkenes.

a.
3-Methylcyclohex-1-ene

b.
Cyclopent-1,3-diene

c. Cyclobutene

5-Methylcyclohex-1,3-diene
d.

e. 2-Methylcyclobut-1,3-diene
An alkenyl group is a noncyclic hydrocarbon substituent
in which a carbon-carbon double bond is present.
LINE-ANGLE STRUCTURAL FORMULAS
FOR ALKENES

 Line-angle formulas for the three- to six-

carbon acyclic 1-alkenes are as follows.
Draw the condensed and line-angle structural
formula for each of the following

 2-Ethylpent--1,4-diene
 2-ethylpent-1-ene
 2,3-dimethylbut-1-ene
 2,3,4 – trimethylhex-1-ene
 2-ethyl-3,4-dimethylpent-2-ene
 CONSTITUTIONAL ISOMERISM IN
ALKENES

Two types of Constitutional Isomerism

 Positional isomers
 Skeletal isomers
 Positional isomers are constitutional isomers with the
same carbon-chain arrangement but different
hydrogen atom arrangements as the result of
differing location of the functional group present.

 Skeletal isomers are constitutional isomers that

have different carbon-chain arrangements as well
as different hydrogen atom arrangements
To determine whether an alkene has cis and trans isomers, draw
the alkene structure in a manner that emphasizes the four
attachments to the double-bonded carbon atom
Cis–trans isomerism is not possible when one of the
double-bonded carbons bears two identical groups.
PHYSICAL PROPERTIES OF ALKENES
AND CYCLOALKENES

 The general physical properties of alkenes and

cycloalkenes include insolubility in water,
solubility in nonpolar solvents, and densities
lower than that of water.

 The melting point of an alkene is usually lower

than that of the alkane with the same number
of carbon atoms.
PHYSICAL PROPERTIES OF ALKENES
AND CYCLOALKENES

 Alkenes with 2 to 4 carbon atoms are

gases at room temperature.
Unsubstituted alkenes with 5 to 17
carbon atoms and one double bond are
liquids, and those with still more carbon
atoms are solids.
 POLYMERIZATION OF ALKENES:
ADDITION POLYMERS

 A polymer is a large molecule formed by the repetitive

bonding together of many smaller molecules.

 The smaller repeating units of a polymer are called

monomers. A monomer is the small molecule that is
the structural repeating unit in a polymer. The process
by which a polymer is made is called polymerization.
An addition polymer is a polymer in which the
monomers simply “add together” with no other
products formed besides the polymer.

The simplest alkene addition polymer has

ethylene (ethene) as the monomer. With
appropriate catalysts, ethylene readily adds to
itself to produce polyethylene.
Using this notation, we have, for the formula of polyethylene,
NATURALLY OCCURING
ALKENES
 A pheromone is a compound used by insects (and
some animals) to transmit a message to other
members of the same species.

The sex attractant of the female silkworm is a 16-carbon

alkene derivative containing an —OH group. Two double
bonds are present, trans at carbon 10 and cis at carbon 12.
A terpene is an organic compound whose carbon
skeleton is composed of two or more 5-carbon
isoprene structural units. Isoprene (2-methyl-1,3-
butadiene) is a five-carbon diene.
NO REGRETS: An Alkene Quiz
1 2 3 4

5 6 7 8

9 10 11 12
Question
It is a cyclic unsaturated hydrocarbon that
contains one or more carbon-carbon
double bond within the ring system.
CYCLOALKENE
Question
Assign an IUPAC name to each of the following
unsaturated hydrocarbons.

But-2-ene
Question
It is a constitutional isomer with the same carbon-
chain arrangement but different hydrogen atom
arrangements as the result of differing location of
the functional group present.

POSITIONAL ISOMERS
 Question
Assign an IUPAC name to each of the following
unsaturated hydrocarbons.

2-­methylhex-3-ene
DANGER!
Switch points with the current
highest scored group.
 Question
Assign an IUPAC name to each of the following
unsaturated hydrocarbons.

Oct-1,5-diene
 Question
TRUE OR FALSE?

But-1-ene has a density greater than that of water.

FALSE
Question
TRUE OR FALSE?

Hex-1-ene has a higher boiling point than but-1-ene.

TRUE
DANGER!
Switch one member of the group with
another member of the other group.
DANGER!
Switch points with the current
highest scored group.
DANGER!
Copy the picture in 10 seconds:
Question
What are the common names of the first
two simplest alkenes?

ethylene and propylene